2-(Naphthalen-1-yl)-4-(naphthalen-1-yl­methyl­idene)-1,3-oxazol-5(4H)-one

Gündoğdu, C.; Alp, S.; Ergün, Y.; Tercan, B.; Hökelek, T.

doi:10.1107/S1600536811015340

Volume 67
Part 5
Pages o1258-o1259
May 2011

Received 21 April 2011
Accepted 22 April 2011
Online 29 April 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.136
Data-to-parameter ratio = 17.5
Details

2-(Naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4H)-one

Cevher Gündogdu,^a Serap Alp,^a Yavuz Ergün,^a Baris Tercan ^b and Tuncer Hökelek ^c ^*

^aDokuz Eylül University, Faculty of Arts and Sciences, Department of Chemistry, Tinaztepe, 35160 Buca, Izmir, Turkey,^bKarabük University, Department of Physics, 78050, Karabük, Turkey, and ^cHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title compound, C₂₄H₁₅NO₂, the oxazole ring is oriented at dihedral angles of 10.09 (4) and 6.04 (4)° with respect to the mean planes of the naphthalene ring systems, while the two naphthalene ring systems make a dihedral angle of 4.32 (3)°. Intramolecular C-HN hydrogen bonds link the oxazole N atom to the naphthalene ring systems. In the crystal, intermolecular weak C-HO hydrogen bonds link the molecules into centrosymmetric dimers. [pi] - [pi] contacts between the oxazole and naphthalene rings and between the naphthalene ring systems [centroid-centroid distances = 3.5947 (9) and 3.7981 (9) Å] may further stabilize the crystal structure. Three weak C-H [pi] interactions also occur.

Related literature

For the roles of oxazolones in the syntheses of amino acids, peptides, antimicrobial or antitumor compounds, immunomodulators, heterocyclic precursors for biosensors coupling and/or photosensitive composition devices for proteins, see: Gottwald & Seebach (1999); Meiwes et al. (1997); Martinez et al. (1964); Gelmi et al. (1997); Croce et al. (1994); Cannella et al. (1996); Kojima et al. (1998). For applications of the 5-oxazolones, including their use in semiconductor devices because of their promising photophysical and photochemical activity, see: Gündogdu et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₄H₁₅NO₂
M_r = 349.37
Monoclinic, P 2₁ /c
a = 18.6927 (5) Å
b = 6.0646 (2) Å
c = 15.6262 (5) Å
= 107.212 (2)°
V = 1692.11 (9) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.42 × 0.35 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.964, T_max = 0.986
29257 measured reflections
4260 independent reflections
2911 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.136
S = 1.07
4260 reflections
244 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C1-C3/C8-C10, C3-C8 and C15-C19/C24 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C2-H2N1	0.95	2.34	3.0110 (19)	127
C10-H10O2ⁱ	0.95	2.46	3.324 (2)	152
C11-H11O2ⁱ	0.95	2.47	3.3601 (18)	155
C23-H23N1	0.95	2.25	2.908 (2)	126
C9-H9Cg4ⁱⁱ	0.95	2.87	3.543 (2)	129
C18-H18Cg1ⁱⁱⁱ	0.95	2.61	3.381 (2)	139
C20-H20Cg2ⁱⁱⁱ	0.95	2.75	3.450 (2)	131
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5196 ).

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of the diffractometer.

References

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organic compounds